Tobacco



finite rates 3,217,717 TOBACCO Donald L. Roberts, Winston-Salem, N.C., assignor to R. J. Reynolds Tobacco Company, Winston-Salem, N.C., a corporation of New Jersey No Drawing. Filed Oct. 25, 1963, Ser. No. 318,793 8 Claims. (Cl. 1131-17) This invention relates to tobacco and has for an object the provision of a tobacco composition having an improved aroma and flavor.

It is well known in the tobacco art that the domestic tobaccos which are exemplified by burley, Maryland, flue-cured, bright leaf or Virginia tobaccos are low in flavor as compared with so-called oriental or aromatic tobaccos which are imported from Turkey, Greece, Bulgaria, Yugoslavia, Rhodesia and Russia. Accordingly, it has been common practice in the tobacco industry to prepare blends of domestic and oriental t-obaccos in order to provide cigarettes which have desired flavor and aroma characteristics. Accordingly, it is a further object of this invention to provide a domestic tobacco which has an enhanced flavor and aroma.

An additional object of this invention is to provide a tobacco which has been treated in such manner as to impart a subtle fiavor which is pleasing to the smoker.

In accordance with one embodiment of this invention a domestic tobacco is provided to which has been added a small amount of 4,4a,5,6-tetrahydro-4,4,7-trimethyl- 2(3H)-napthalenone. The above chemical, herein referred to as compound I, may be represented by the following formula:

GI-I O a The chemical compound I indicated above can be synthesized from -oxodihydro-a-ionone by means of an intramolecular aldol condensation using sodium methoxide.

A detailed description of the synthesis of compound I is as follows:

A. Dihydro-u-ionone (85 grams) prepared by hydrogenation of u-ionone as is known, was oxidized by contacting with t-butyl chromate in benzene solution for a period of four days at room temperature. Chromatography of the products from the oxidation yielded grams of dihydro-a-ionone, 3 grams of 4-oxodihydro-,6- ionone, 10 grams of S-OXOClihYdlO-a-iOl'lOHE, and other side products.

B. A S-gram sample of 5-oxodihydro-a-ionone, prepared as above, was dissolved in milliliters of methanol containing 5 percent sodium methoxide. After standing overnight the solution was neutralized and extracted with ether. The dried ether solution was evaporated and the crystalline residue (compound I) (4.5 grams) recrystallized from methanol.

Compound I is a solid having a melting point of 97 C. (from methanol) and the following characterization:

Ultraviolet spectrum: A532, 292 m (e=26,200)

Infrared spectrum: 1653, 1635, 1595, 1370, 1290, 1194, 1142, 1016, 953, 928, 903, and 840 cmf NMR spectrum: T=3.90(1), 422(1), 7.68(2), 7.82 (2), 807(3), 887(3), and 910(3).

Analysis.Calcd. for C H O: C, 82.06; H, 9.54; mol. wt., 190. Found: C, 81.98; H, 9.52; mol. wt., 190 (mass spectrum).

Patented Nov. 16, 1965 In accordance with this invention, the designated compound I is usually added to a domestic tobacco in amounts to provide a tobacco in which is dispersed about 0.001 to about 1.0 percent by weight of the additive. Preferably the amount of additive is between about 0.005 and about 0.03 percnet by weight in order to form a domestic tobacco having a desired flavor and aroma. The preferred percentages may be somewhat less, however, if other flavorants imparting a desired aroma are also employed. The additive may be applied in any suitable manner and preferably in the form of a liquid solution or suspension by spraying, dipping or otherwise. The additive may be incorporated at any step in the treatment of the tobacco, but is preferably added after aging, curing and shredding and before the tobacco is formed into cigarettes. Likewise, it will be apparent that only a portion of the domestic tobacco need be treated and the thus treated tobacco may be blended with other tobaccos before the cigarettes are formed. In such cases, the tobacco treated may have the additive in excess of the amounts above indicated so that when blended with other tobaccos the final product will have the percentage within the indicated range.

In accordance with one specific example of this invention, an aged, cured and shredded burley tobacco is sprayed with a one percent ethyl alcohol solution of the above indicated compound in an amount to provide a tobacco composiiton containing 0.01 percent by weight of the additive on a dry basis. Thereafter the alcohol is removed by evaporation and the tobacco is manufactured into cigarettes by the usual techniques. The cigarette when treated as indicated has a desired and pleasing aroma which is detectable in the main and side smoke streams when the cigarette is smoked; this aroma is described by some smokers as a pleasant woody note.

It will be particularly apparent that the manner in which the additive is applied to the tobacco is not particularly important since, as indicated, it may be done in the form of spraying or dipping, utilizing suitable suspensions or solutions of the additive. Thus, water or volatile organic solvents, such as alcohol, ether, acetone, volatile hydrocarbons and the like, may be used as the carrying medium for the additive while it is being applied to the tobacco. Also, other flavor and aroma producing additives, such as those disclosed in Jones United States Patent No. 2,766,145 and Schumacher United States Patent No. 2,978,365, may be incorporated into the tobacco with the additives of this invention.

While this invention is particularly useful in the manufacture of cigarette tobacco, it is also suitable for use in connection with the manufacture of pipe tobacco, cigars and other tobacco products formed from sheeted tobacco dust or fines which are Well known to the art. Likewise, the additives of the invention can be incorporated with materials such as filter tip materials, seam paste, packaging materials and the like which are used along with tobacco to form a product adapted for smoking.

Those modifications and equivalents which fall Within the spirit of the invention and the scope of the appended claims are to be considered part of the invention.

I claim:

1. A domestic tobacco having added thereto a small amount of 4,4a,5,6-tetrahydro 4,4,7 trimethyl-2(3H)- napthalenone sufiicient to alter the flavor of the tobacco.

2. A domestic smoking tobacco having added thereto between about 0.001 and 1.0 percent by weight of 4,4a,5, 6-tetrahydro-4,4,7-trimethyl-2 (3H) -napthalenone.

3. A tobacco product having added thereto a small amount of 4,4a,5,6-tetrahydro 4,4,7 trimethyl-2(3H)- napthalenone sufiicient to improve the flavor of the tobacco.

4. A product adapted for smoking having added thereto a small amount of 4,4a,5,6-tetrahydro-4,4,7-trimethy1- 2(3H-naptha1enone suflicient to improve the flavor of the smoking product.

5. A tobacco product having added thereto between about 0.001 and 1.0 percent by weight of 4,4a,5,6-tetrahydro-4,4,7-trimethy1-2(3H)-napthalenone.

6. A tobacco product having added thereto between about 0.005 and 0.03 percent by weight of 4,4a,5,6-tetrahydro 4,4,7-trimethy1-2 (3H) -naptha1enone.

7. A product adapted for smoking having added thereto between about 0.001 and 1.0 percent by weight of 4,4a,5,6-tetrahydro-4,4,7-trimethy1-2 3H) -naptha1enone.

8. A product adapted for smoking having added thereto between about 0.005 and 0.03 percent by weight of 4,4a,5,6-tetrahydro-4,4,7-trimethy1-2 3H) -napthalenone.

References Cited by the Examiner UNITED STATES PATENTS 583,719 7/1897 Tiernann 261587 1,933,939 11/1933 Smith 261-587 2,977,254 3/1961 Rosenberg et a1 13117 3,118,452 1/1964 Mosby 131-17 ABRAHAM G. STONE, Primary Examiner.

P RAY CHAPPELL, Examiner. 

1. A DOMESTIC TOBACCO HAVING ADDED THERETO A SMALL AMOUNT OF 4,4A,5,6-TETRAHYDRO-4,4,7-TRIMETHYL-2(3H)NAPTHALNONE SUFFICIENT TO ALTER THE FLAVOR OF THE TOBACCO. 